That Could've Gone Better
by XCgirl
Summary: Wash gives Simon advice about Kaylee. Simon tries to take it, but somehow, every one of the members of the crew tends to have a moment where things could've gone a lot better, and the doctor is no exception. If this needs an M rating PLEASE let me know!


A/N: Finally I've found something worth posting! Hope you like it! This was based off of two different episodes, Jaynestown and another one I can't remember the name of...anyway, the scene with Shepherd Book was straight from the Episode with the Forgotten Name; afterwards is just my take on what should've happened after :)

**Disclaimer: I am not Joss Whedon. I therefore own none of the characters mentioned, nor the TV series that was so shamefully canceled.**

* * *

"So tell me, Simon, talked to Kaylee lately?" Wash asked amicably as Simon readied a vitamin injection.

"I don't think I know what you're talking about," Simon feigned indifference in his usual detached, soft-spoken doctorly way.

Wash gave him a look. "Really? From one head-over-heels man to another, you're too obvious not to know what I'm talking about. Kaylee's a sweet girl, and it's nice to know you have good taste, but OW!"

"Sorry. I forgot to say it's gonna hurt."

Wash gingerly rubbed the spot where he'd been stuck with the needle. "You know, Doc, Kaylee likes you plenty, and you're the only thing stopping anything from happening between you two."

Simon leaned back against the tiny infirmary's counter, peeling off his glove. "So you're saying I…should sleep with Kaylee?"

"Ta ta ta ta TA! I did NOT want the conversation to go there!" Wash cringed and shuddered.

"But…you took it there, Wash…" Simon replied, trying to reason out the conversation with as little awkwardness shown on his part.

"No! Well, indirectly, yes. Look, the idea of Kaylee doing, well, _that_ doesn't sit right with the rather disturbing images coming to mind right now, but the point is…" Wash shivered. "The point is, she makes you loosen up. You aren't as stiff when she's around, even more than with River, and a hell of a lot more awkward. And Shepherd's God only knows how this is even possible, but she smiles _a lot_ more when she's around you. Kaylee's not exactly the flustery type, but she giggles and blushes when you're around. She reminds me of a happier, smilier, girlier, innocent…er version of Zoe when she finally started coming around for me." Wash couldn't hide the ghost of a grin from escaping at the memory.

"So…what are you saying I should do?"

Wash turned in the doorway, gesturing as if it were obvious. "Talk to her. Alone. Telling people how you feel in this kind of a situation usually has a pretty good effect. Hell, it worked on Zoe." He left, discreetly shutting off the comlink in his pocket after turning the corner.

"Five bucks says he won't do it," Mal wagered as Wash entered the bridge.

"Sir, we don't have bucks anymore," Zoe said stoicly.

"Figure of speech. He's not gonna do it," Mal asserted.

Wash looked hurt. "Come on, you don't think I did well enough? I thought I did great."

The other two ignored him. "Sir, I thought you had some kinda policy against shipboard romances. I distinctly remember your objections to Wash and me."

"I do. I'm just tired of seein' little Kaylee get her hopes up and shot down again. And we all know the doc is so tightly wound all the time he's bound to have some kinda break down eventually. The last thing we need is another mental onboard and one less doctor to treat 'em, and Kaylee seems to be pretty good at calmin' him down. And you two…well, you two don't follow orders as well as them."

* * *

"Kaylee?" Simon squinted in the low light of the engine room.

"Over here," Kaylee's head popped up on the other side of the generator. "Watcha doin' down here, Doc? You're gonna get your suit all greasy," she asked cheerfully.

"I, uh, I couldn't sleep, and I saw the light was on in here." He paused, trying to think of something to say. "Um…how-how's Serenity?"

"She's doin' great! Her right couple and converter coil were gettin' a little gummed up again, but I just finished cleanin' her up." She scooted out of the space under the engine where she'd been working and faced Simon, who by now had crossed the engine room to her side.

"Oh. So, uh, are you…going to bed now?" _No, Simon, she was going to go up and ask Inara for beauty tips. What else would she be doing now?_

"Well yeah," she grinned, "just soon as I wash all the grease off." There was a thick swath of it running from her cheek down her jaw line. "Goodnight, Serenity." She patted the engine and tried to pass Simon, but he caught her hand.

"Kaylee…" Her face was curious, open, innocent.

"Yeah, Doc?"

"I…" _Come on, Tam, think, gorram it!_ "Remember when we were in the town where everyone thought Jayne was a hero? In the pub?"

She dimpled, pulling part of the grease streak into shadow. "Uh-huh."

Simon hesitated. _Stop being so awkward, Tam! Man up!_ "I…it wasn't the alcohol talking. You're really…pretty. Especially when…" he reached up and bashfully smoothed the grease on her cheek away, "especially when you're covered in engine grease." He smiled shyly, kicking himself for having possibly gone too far.

Kaylee let out a tiny burst of nervous laughter, a huge frozen smile of shock plastered on her face. "G-goodnight, Simon," she stuttered with a blush. She shot around the corner, and Simon kicked himself again, cursing repeatedly.

"Yep. That could've gone better," he muttered.

* * *

"But…ain't there anything here that's worth stayin' for?" Kaylee asked quietly, pleading for a positive answer without a word.

Simon's throat closed up as he realized what she was really asking. _Yes!_ his brain screamed. _Yes! You!_ _You!_ But he couldn't say it, even as her face began to crack and crumple and harden against him. Not again. He couldn't have her mad at him for screwing up _again_. Before he knew it, his hand was at her cheek, brushing her hair over her shoulder. He was leaning in…

And Shepherd Book turned the corner, eyes trained on a book. " 'Scuse me," he mumbled as he brushed between them and up the ladder, eyes never looking up. Simon bit his lip, willing himself not to curse a Shepherd.

"Oh. Well. Um, goodnight," Kaylee gulped.

"Yeah. Goodnight." She turned away. Simon kicked himself yet again, then turned and followed her down the hall, not breaking stride as she turned from her bunk's doorway and opened her mouth in confusion.

"Sim— " Without skipping a beat he leaned down and kissed her full on the mouth, taking her face in his hands and massaging her cheekbones with his thumbs.

Kaylee stumbled backwards, not believing what was happening and kissing back nonetheless. If Simon had lost it, she might as well take advantage of it while she could.

Simon pulled back tentatively, regaining enough sense to realize what he was doing. It wasn't enough to convince him to pull his forehead from hers.

"Simon?" Kaylee asked, hardly allowing herself to hope he hadn't gotten whatever it was River had and that he actually meant that. "Are you okay?"

"Uh, uh, yeah," he half-whispered, delirious and reveling in the fact she hadn't pulled away yet.

"Um," she smiled, "so you finally came around." She gave a slightly nervous giggle.

"Yeah, yeah I did." Simon's brain, in all its genius, couldn't come up with anything witty or romantic to say, not while he was close enough to smell the traces of engine grease she hadn't managed to wash out of her hair. Wash. He'd be so proud.

Simon nearly choked when she finally pulled away, climbing down into her bunk. He sank against the wall, stomach and heart dropping to the floor with him. He'd made his move, and all it had done was prove a suspicion of hers. Shepherd's God, he was an idiot…

"Simon?" Kaylee's head popped out of the opening with a shy smile. "Are…are ya comin'?" She bit her lower lip, nervous. He was pretty shy, after all…

Simon looked down either hallway. "Are you sure about this, Kaylee?" The rest of the crew was asleep, as far as he knew; River was, too…

She hesitated, a slow smile creeping onto her face. "Uh-huh."

Wordlessly, Simon climbed down, a fleeting thought of what Wash would say if he knew passing from his mind as Kaylee stretched up to kiss him again.

Up in the cockpit, Wash smiled, pleased with himself as long as he didn't think of what was going on in Kaylee's room tonight. "Yup," he murmured. "That went well."

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**So? What yall think? Like it? Hate it? Needs work? Review and let me know!!**


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